Developing moral imagination is a central yet challenging learning outcome for students in professional education programs for fields including engineering. This paper introduces theories of moral imagination in early Confucian ethical thought and explores what implications can be drawn from these theories for engineering ethics and professional education. Rather than appealing to pre-determined principles, early Confucians advocated a moral particularism and argued that moral actors need to exercise their imaginations to discern diverse factors and constraints present in moral situations. They need to “extract” from moral situations possible reasons for certain actions. Texts such as the Analects should be read as manuals or logs of decision-making rather than as prescriptive guidance or descriptive anecdotes. The moral actions we take in different situations are influenced by the special roles we play in these situations. The nature of a particular role relationship often evokes feelings and expectations characteristic of that relationship. Cultivating and educating our imaginations allows us to draw on diverse human abilities, assess multiple moral strategies, and identify the most suitable (rather than simply calculating “the best”) option that helps to activate our moral selves and grow our relationships with others. Early Confucians proposed a variety of methods for developing moral imaginative capabilities including reflective observation of social interactions, moral thought experiments, analogical extension of familial relations, and the “as-if” rituals. This paper ultimately considers the possible implications of these theories for teaching and learning ethical conduct in engineering, given the increasing interest of the engineering profession in humanitarian engineering and cross-cultural collaboration and the two fields of engineering practice often encompass incomplete knowledge and diverse values.